


The Boss

by EverythingsAvengers



Category: Supernatural
Genre: Begging, Boss/Employee Relationship, Bottom Dean, Butt Plugs, Coming Untouched, Dean in Panties, Dom Castiel, Dom/sub Undertones, Gay Sex, Light BDSM, Lingerie, M/M, Panty Kink, Sub Dean, Top Castiel, Voice Kink
Language: English
Status: Completed
Published: 2015-08-01
Updated: 2015-08-01
Packaged: 2018-04-12 11:10:03
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,297
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4477082
Author URL: https://archiveofourown.org/users/EverythingsAvengers/pseuds/EverythingsAvengers
Summary: <blockquote class="userstuff">
              <p>Dean Smith knows that the crush he has on his new boss is inappropriate, but that doesn't change that fact that Castiel is gorgeous and has a voice that makes Dean weak in the knees. So when Cas asks him out with a note and a gift that makes Dean strain in his dress pants, it's really not his fault that he can't say no.</p>
            </blockquote>





	The Boss

Dean Smith is a logical, sensible man. He thinks thing through, and he works hard. Always. He’s busted his ass to get to where he is at Sandover.

Director of Sales and Marketing.

It’s got a nice ring to it, and a nice paycheck, which definitely doesn’t hurt. He has a nice car and an even nicer apartment. He’s proud of where he’s gotten to.

Which is why he can’t for the life of him figure out why he’s trying to throw it all down the drain.

Because Dean’s pretty sure mercilessly flirting with your boss can get you one of two things. Either 1. Sexual harassment charges or 2. Fired

And he’s really not sure which is worse.

But he can’t help it. Ever since Castiel Novak because COO (Chief Operating Officer) of Sandover Bridge & Iron Inc. Dean has thought about him more than any of his work. He was starting to think that if the flirting didn’t get him fired his decline in proficiency definitely would.

And he was everywhere. No matter when Dean went he seemed to be met with dark brown sex hair and beautiful blue eyes. He just couldn’t escape them.

If Dean was being honest with himself he would admit that he didn’t want to escape that amazing stare. That’s why he jumped on every opportunity to talk to him.

At first it was about work and sales and spreadsheets, boring things, really, but Dean just wanted to hear that gravelly voice no matter what he was saying. And then I was about how Dean was thinking about trying a cleanse. (That was when Dean learned that Cas could never give up burgers, even if it was only for a couple weeks.)

He also learned that Cas went to Berkeley and graduated the same year Dean started at Stanford. Dean also learned that for exercise he likes to run. (Dean made a comment about how that explained why he had such a nice ass that had Dean kicking himself for the rest of the day.)

And that’s how it pretty much went for a couple weeks. They flirted (or Dean flirted) and then he beat himself up for how unprofessional he was being before going home and masturbating with his bosses face at the forefront of his mind.

That was until Friday morning came and Dean found a box waiting for him on his desk.

It looked like a present; a plain black box with a lid and a blue ribbon held it closed. But instead of a ribbon on top there was a note with his name written neatly on the front: _Dean Smith_

He pulled the letter off and opened it as he sat down at his desk.

_If you would have me I would like to take you to dinner tonight._  
If you decline please ignore this extremely unprofessional request and leave the box (unopened please) on my desk.  
But if you would like to go email me your address and I will pick you up at seven tonight.  
And if you do accept my offer feel free to keep this gift.  
  


_Eagerly awaiting your answer,_ _C. Novak_

_p.s. you should probably open your present away from prying eyes_

He couldn’t help but smile at the small, neat, perfect handwriting; his finger brushing over the beautiful signature. Then it started to set in that Cas just asked him out.

In his own cute, but very formal way, Castiel just asked Dean on a date and he wasn’t sure how to answer.

Sure Dean wanted to say yes. He wanted to say yes more than anything. It had been a while since he’d gone on an actual date considering he spent most of his time working and he’d never been one for random hookups.

Not to mention he really liked Castiel.( Not just because he was ridiculously attractive either.)

But this guy was his boss and this would be wrong on so many levels and really should just do the right thing and say no.

That didn’t stop Dean from opening up his email and sending a quick: _I would love to._ He quickly typed in his address and hit send before he could stop himself.

Then, finally, Dean looked over at the box with the pretty blue ribbon.

The note said to open it away from prying eyes and since there was no one around but him he figured now would be a pretty safe time to do it.

He was wrong.

After pulling off the ribbon he slowly pulled the top off. He caught a glimpse of pink lace before he slammed it closed.

“Fuck,” he muttered, his pants getting tighter by the second.

They hadn’t even gone on a date yet and somehow Cas knew about his panty kink. _How the hell-_

His computer beeped, alerting him of a new message. Dean took a deep breath before opening the message.

_Dean,_  
I’m glad you agreed to go out with me. I can’t wait to see you tonight. There’s this real nice restaurant I want to take you to (no burgers) but I hope you’ll like it.  
And I hope you like your gift. I would love for you to wear all of it tonight. Oh, and a suit and tie. (Formal wear is required.)  
I’ll see you at seven,  
C. Novak 

To say Dean was on edge for the rest of the day would be an understatement.

He spent all day somewhere between anxious and aroused. He’d hidden the box in his desk drawer, untouched, since the first time. But Dean saw (at least partly) what was in it and he couldn’t stop thinking about it.

Or the email Castiel sent him that said he wanted him to wear it. He was more turned on that he could ever remember being. He felt like a teenager all over again and it sucked.

Finally the end of the workday came and Dean practically ran out to his Prius, the box tucked under his arm.

Dean realized something as he looked through his wardrobe. He had virtually none that were just black and white. All of his shirts were either colored or striped or patterned, it took him almost half an hour to find a plain white shirt and it was almost too small on him, but it would have to do.

Then he grabbed some black pants and a black jacket, throwing them on the bed along with the shirt before searching for a tie. He was about to call it quits and wear a colored one when he finally found a solid black one at the bottom of his drawer.

He checked his watched and decided he still had plenty of time to grab a quick shower before Cas arrived.

When he walked out after his shower though, a towel around his waist, he was met with that box. It was sitting in the center of his bed, clothes piled around it, seemingly innocent, but Dean knew better.

Dean, almost reluctantly, picked it up and sat down with it.

When he pulled the top off his whole body froze for a second. It seemed like his body couldn’t decide where it wanted the blood to flow more, to his face or cock.

Inside was the pink lacey things he saw originally, but also pink and black stockings and a matching corset. But what really get Dean’s attention was the sizeable black plug sitting on top.

He wasn’t sure how he’d missed that originally, but it didn’t matter, it was still there right on top teasing him. And for some reason he felt like that was exactly what Cas was doing. He wanted to see if Dean would actually wear not only the lingerie, but the plug to their dinner and for some reason Dean really wanted to do what Cas wanted.

Dean pulled the bottle of lube out from his dresser and took his towel off. He laid the towel down before sitting onto it (not wanting get lube on his sheets) and picking his feet up onto the bed.

He didn’t let himself get too into it, he still had to get dressed, but he was rock hard as he finally slipped in the plug. It was much bigger than his fingers and a little bit of a stretch, but it was a pleasant fullness that he hadn’t had in a while.

As he pulled the panties on he tried to coerce his boner down but without much luck. It didn’t help that when he sat down to pull the stockings on the plug got pushed even deeper into his ass.

Dean was almost thankful for the corset. It took a lot more time and effort to figure out how to put on than he’d anticipated, but it was enough time for him to calm down enough for him to only be half hard as he looked himself over in the mirror.

And _fuck_ he looked good. Dean twirled around to see the base of the plug peeking from between his cheeks, a strip of pink lace doing next to nothing to help cover it.

He spent another minute looking at himself before realizing that he _really_ had to finish getting dressed.

He’d just finished lacing up his shoes when Cas got there.

Cas who was wearing a perfect tailored Italian style suit that fit his slightly muscled, slim figure perfectly. If Dean didn’t know any better he would almost say it was a Zegna, but those a full suit could be over twenty thousand (and Cas was wearing a vest and everything).

He tried not to think about it as Cas walked him down to his car. A pretty nondescript looking black car that Dean realized was actually an Aston Martin DB9, which is easily a hundred and eighty thousand dollar car.

_Okay,_ Dean thought, _maybe I was wrong about this guy having money._

“Nice car,” Dean commented as Cas started it up. “Thanks,” he answered with a shrug. “It’s an okay car, but I have something better.”

“Better than this?”

Cas laughed, “Yeah. Maybe I’ll show you some time.”

That’s how it goes through out the car ride and long into their date. The food looks as good as it tastes and Dean’s pretty sure it’s the most expensive food he’s ever eaten (and most delicious) which he says multiple times throughout.

Finally it gets to him though and he can’t ignore the fact that they’re both ignore Dean ‘present’ and Dean ignoring the fullness in his ass and the tightness in his pants.

“Why did you want me to wear the plug?” Dean blurts out before he can stop himself. His cheeks flushing as he looks around hoping no one heard him, but they’re all too engrossed in their own conversations to notice him.

Cas seems amused by the question. He leaned in close, talking in a voice barely over a whisper when he said, “Well, if you would like to go home with me I would like to fuck you senseless as soon as you walk through the door.”

To say that dinner couldn’t end quickly enough was an understatement.

As they (finally) walked outside Cas asked, “Your place or mine?”

Okay so he actually said, “Would you like to go to my place or would you like for me to take you home?”, but still it was basically the same thing.

But as Dean thought about it, it really wasn’t the same thing. There was only one scenario where he was going to get laid tonight and they both knew it. The double meaning in his question was glaringly obvious and Dean hadn’t taken the time to dress up just to go back home.

So he nodded, “Your place would be fine,” he answered.

Dean felt like he was on the edge of his seat the entire ride back to Cas’ apartment.

They finally took the elevator up to (of course) the top floor. Dean figured by now he shouldn’t be surprised that Castiel had the pent house suite.

It still seemed like too much for even the COO of Sandover to be able to afford, but he didn’t want to worry about that right now when Cas’ hand is trailing up and down his back as they watch the floor numbers creep by.

Neither of them spoke as Cas unlocked his apartment door, but as promised as soon as they walked in Cas pushed him into the door with a kiss.

Dean moaned into his mouth immediately grasping at Cas’ suit trying to find purchase. Trying to still his shaking hands as Cas leaned down to kiss at his neck.

“Did you wear the plug for me?” Cas asked into his ear.

Dean shivered at his tone as he nodded vigorously, unable to talk. Cas started pulling off Deans jacket and he let him; moving away from the door slightly so he could pull it off.

“Of course you did,” Cas stated softly, “You’re so good for me. I bet you put the panties and all on for me, didn’t you?” Dean nodded again, “Yes,” he whispered as Cas grabbed onto his ass, hard. The plug jostled around in his ass and Dean leaned his head back with a groan against the door.

With that Cas practically picked him up and dragged him into the bedroom. Which apparently was through the living room and down a long hallway (too far away in his opinion).

When the finally arrived at their destination though Cas didn’t jump on him like before instead he pushed Dean into the edge of the bed and then walked away slowly, throwing his jacket off and onto the dresser facing the bed.

Dean stood where he was, unsure what to do. His whole body was buzzing with energy, he was on edge and extremely horny. His cock was straining against his pants; it was just this side of painful, but he couldn’t do anything but stand there staring at Cas as he looked him over.

 “Strip,” Cas finally ordered.

Dean’s hands were shaking as he slowly undid his buttons one at a time. He threw the shirt down beside him and then kicked off his shoes before slowly sliding his pants down too. The belt fell loudly onto the hardwood floor, echoing in the extremely quiet room.

He felt naked now standing there in nothing but the soft pink lingerie, with Cas’ eyes roaming over him. While Dean was getting undressed Cas rolled up the sleeves and now he slowly undid his belt, never breaking eye contact.

As he finally pulled his cock out of his dress pants he said, “Turn around.” Dean just stared, confused for a second before turning to face the bed.

He watched out of the corner of his eye as Cas walked around to his bedside table to pull out a condom and a small bottle of what Dean assumed to be lube. The only light was drifting in from the bathroom.

Cas slid the condom on and then lathered his now covered cock with the lube before turning to look at Dean. “Bend over,” he commanded as he walked up behind him.

Dean complied and was rewarded with Cas hands on his hips, pulling on the lace and then running up and onto the back of the corset. Dean moaned into the sheets; his whole body shivering.

Cas hummed behind him as he pulled the thong to the side. “You look so beautiful,” Cas whispered, grabbing onto the base of the plug before slowly pulling it all the way out and then pushing it back in again.

He pulled it, again, out and then in, Dean’s now dry hole protesting slightly. “Cas, please,” Dean moaned, pushing back against him.

Cas just hummed again before finally pulling the plug out. “Look at you,” Cas said, breathless, “All open and ready for me.” Dean felt him start to push in, ever so slowly, before finally bottoming out.

But he didn’t move. He just stood there, filling Dean up completely, before pulling completely out and pushing back in just as slowly as before.

“I thought I was going to get fucked,” Dean groaned, irritated, but Cas didn’t seemed fazed. He just chuckled and stopped moving completely.

“Then come on,” Cas said slapping Dean’s ass, “Fuck yourself on my cock.”

Dean moaned but did start moving back onto Cas, slowly fucking himself before getting a rhythm. It felt like maybe he should feel weird about this. Humiliated maybe. He was still fully clad in the lingerie, his thong just pushed to the side by Cas. His cockhead sticking out the top and leaking onto the bed below him. But it was next to impossible to feel anything but good when Cas was saying nothing but praise above him.

Saying how beautiful he looked, how amazing he was, how good he was, and he was saying all of this in that gravely sex voice that did thing to Dean. He was just starting to understand why some people had voice kinks.

Dean was pushing himself back, faster and faster, but it just wasn’t enough. He couldn’t get the right angle or the right speed and he just needed more.

“Cas,” Dean tried to say, his voice low and cracking the whole way, “Please.”

Thankfully he didn’t have to say anything else because Cas seemed to understand what he needed. He grabbed Dean’s hip with the hand that wasn’t pushing his panties to the side and pushed Dean into the bed with his first thrust.

Dean pressed his whole body flush against the mattress as Cas set an unforgiving pace, hitting his prostate constantly. He could barely move, barely keep up as he tried to meet Cas’ thrusts and rut against the mattress underneath him.

He came quicker than he would have liked, but didn’t feel as bad when he felt Cas losing his rhythm, knowing he would be following right after.

When Cas finally did come it was with a low moan that sounded suspiciously like Dean’s name.

As Dean came down from his post-orgasm high Cas tied off and threw away the condom. That was the first time he really noticed that Cas was still fully dressed.

Dean felt naked in comparison.

“Sorry,” he muttered, pointing at the wet spot on the panties and then down at the sheets. Dean figured both of those things were probably very expensive.

Cas didn’t seem bothered by it. “I’ll get them dry cleaned and then you can keep them.” Dean blushed and then shook his head, “No I couldn’t-”

“I got them for you,” Cas shrugged, “I’d like you to keep them.”

Dean could do nothing but nod. Honestly it seemed pretty comical to think of Cas going to some expensive lingerie store to buy him pink lacey panties, but he didn’t say that, instead he allowed Cas to lead him into the bathroom.

Cas slowly undressed him. Unlacing the corset first before pulling it off. The stockings were next; Cas pulling him onto the counter to pull them off one by one. All of this seemed strangely intimate.

Compared to what they just did it seemed weird that Cas doing nothing more than undressing him would be this intimate, but this felt closer than he’d ever been to another partner as Cas washed him in the shower.

Running shampoo through his hair and then conditioner before lathering up his whole body with a pomegranate body wash. He felt lighter than he could ever remember feeling as Cas took care up him. Lightly massaging out all of his sore muscles before finally drying off and going to bed.

It was the best Dean had ever slept.

**Author's Note:**

> This is the first really smutty thing I've really ever written, so I hope y'all like it! Please leave some comments and kudos guys!


End file.
